organic compounds
The title compound, C9H7BrN2O, was synthesized by the hydrazinolysis of 2-(4-bromophenyl)oxazolo[3,2-a]pyrimidinium perchlorate. In the molecule, the oxazole and benzene rings make a dihedral angle of 9.68 (7)°. The crystal packing is stabilized by intermolecular N—HN hydrogen bonds and van der Waals forces.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038918/cv2126sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038918/cv21262sup2.hkl |
CCDC reference: 624198
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.049
- wR factor = 0.091
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C3 - C31 .. 7.39 su
Alert level C PLAT030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C34 - C35 .. 5.42 su
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Computing details top
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: WinGX (Farrugia, 1999).
5-(4-bromophenlyl)-1,3-oxazol-2-amine top
Crystal data top
C9H7BrN2O | Dx = 1.761 Mg m−3 |
Mr = 239.07 | Melting point: 494(1) K |
Orthorhombic, Pccn | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2ab 2ac | Cell parameters from 25 reflections |
a = 39.344 (3) Å | θ = 30–33° |
b = 7.5684 (8) Å | µ = 5.88 mm−1 |
c = 6.0571 (8) Å | T = 293 K |
V = 1803.6 (3) Å3 | Plate, yellow |
Z = 8 | 0.12 × 0.12 × 0.02 mm |
F(000) = 944 |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 1644 reflections with I > 2σ(I) |
Radiation source: Fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 75.0°, θmin = 2.3° |
ω scans | h = 0→49 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→9 |
Tmin = 0.539, Tmax = 0.891 | l = 0→7 |
1860 measured reflections | 1 standard reflections every 60 min |
1860 independent reflections | intensity decay: 3% |
Refinement top
Refinement on F2 | Secondary atom site location: Difmap |
Least-squares matrix: Full | Hydrogen site location: Geom |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.091 | w = 1/[σ2(Fo2) + (0.0753P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
1860 reflections | Δρmax = 0.56 e Å−3 |
127 parameters | Δρmin = −0.78 e Å−3 |
4 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: Direct | Extinction coefficient: 0.0021 (2) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
N1 | 0.54417 (4) | 1.04294 (14) | 0.9257 (2) | 0.0558 (3) | |
C2 | 0.57775 (4) | 1.0844 (2) | 0.8783 (2) | 0.0564 (3) | |
H2 | 0.5914 | 1.1563 | 0.9659 | 0.068* | |
C3 | 0.58809 (4) | 1.00773 (16) | 0.6899 (2) | 0.0506 (3) | |
C31 | 0.61903 (4) | 1.00097 (15) | 0.5631 (2) | 0.0491 (3) | |
C32 | 0.61966 (5) | 0.9242 (2) | 0.3553 (2) | 0.0570 (4) | |
H32 | 0.5997 | 0.8783 | 0.2965 | 0.068* | |
C33 | 0.64947 (4) | 0.91436 (17) | 0.2328 (2) | 0.0545 (3) | |
H33 | 0.6498 | 0.8626 | 0.0936 | 0.065* | |
C34 | 0.67899 (5) | 0.98533 (19) | 0.3269 (3) | 0.0551 (4) | |
Br34 | 0.719801 (6) | 0.96763 (4) | 0.15797 (4) | 0.08280 (16) | |
C35 | 0.67923 (4) | 1.06160 (19) | 0.5322 (3) | 0.0611 (4) | |
H35 | 0.6993 | 1.1051 | 0.5924 | 0.073* | |
C36 | 0.64942 (5) | 1.0723 (2) | 0.6463 (2) | 0.0601 (4) | |
H36 | 0.6492 | 1.1284 | 0.7830 | 0.072* | |
O4 | 0.56008 (3) | 0.91160 (13) | 0.61232 (16) | 0.0542 (3) | |
C5 | 0.53553 (4) | 0.94253 (15) | 0.7629 (2) | 0.0521 (3) | |
N5 | 0.50558 (4) | 0.8617 (2) | 0.7307 (3) | 0.0697 (4) | |
H5A | 0.4894 (6) | 0.871 (4) | 0.821 (4) | 0.087 (7)* | |
H5B | 0.5026 (5) | 0.796 (3) | 0.616 (4) | 0.081 (6)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0728 (8) | 0.0441 (6) | 0.0505 (6) | −0.0021 (5) | 0.0025 (6) | −0.0089 (5) |
C2 | 0.0716 (9) | 0.0475 (6) | 0.0501 (7) | −0.0074 (6) | −0.0029 (6) | −0.0031 (5) |
C3 | 0.0740 (8) | 0.0275 (5) | 0.0503 (7) | −0.0002 (5) | −0.0046 (6) | −0.0012 (5) |
C31 | 0.0668 (7) | 0.0299 (5) | 0.0507 (7) | 0.0001 (5) | −0.0027 (6) | 0.0015 (5) |
C32 | 0.0785 (10) | 0.0458 (6) | 0.0467 (7) | 0.0018 (7) | −0.0022 (6) | 0.0068 (5) |
C33 | 0.0813 (9) | 0.0332 (5) | 0.0491 (7) | −0.0060 (6) | 0.0016 (7) | −0.0073 (5) |
C34 | 0.0663 (9) | 0.0405 (6) | 0.0583 (9) | 0.0032 (6) | −0.0027 (6) | 0.0035 (6) |
Br34 | 0.0753 (2) | 0.0885 (2) | 0.0846 (2) | 0.00489 (9) | 0.01464 (9) | −0.00479 (10) |
C35 | 0.0676 (9) | 0.0484 (7) | 0.0673 (10) | −0.0121 (6) | −0.0023 (7) | 0.0006 (6) |
C36 | 0.0736 (8) | 0.0627 (8) | 0.0440 (7) | −0.0025 (7) | −0.0039 (6) | −0.0041 (6) |
O4 | 0.0647 (6) | 0.0478 (5) | 0.0501 (5) | −0.0024 (4) | −0.0002 (4) | −0.0080 (4) |
C5 | 0.0738 (8) | 0.0308 (6) | 0.0516 (7) | 0.0011 (5) | 0.0014 (7) | −0.0021 (5) |
N5 | 0.0746 (8) | 0.0702 (9) | 0.0644 (8) | −0.0149 (7) | 0.0122 (7) | −0.0243 (7) |
Geometric parameters (Å, º) top
N1—C5 | 1.2905 (19) | C33—H33 | 0.9300 |
N1—C2 | 1.388 (2) | C34—C35 | 1.371 (2) |
C2—C3 | 1.343 (2) | C34—Br34 | 1.9089 (19) |
C2—H2 | 0.9300 | C35—C36 | 1.364 (3) |
C3—O4 | 1.4015 (18) | C35—H35 | 0.9300 |
C3—C31 | 1.440 (2) | C36—H36 | 0.9300 |
C31—C32 | 1.387 (2) | O4—C5 | 1.3493 (19) |
C31—C36 | 1.406 (2) | C5—N5 | 1.342 (2) |
C32—C33 | 1.390 (2) | N5—H5A | 0.84 (3) |
C32—H32 | 0.9300 | N5—H5B | 0.86 (2) |
C33—C34 | 1.401 (2) | ||
C5—N1—C2 | 103.06 (13) | C35—C34—C33 | 122.44 (16) |
C3—C2—N1 | 111.47 (14) | C35—C34—Br34 | 120.66 (13) |
C3—C2—H2 | 124.3 | C33—C34—Br34 | 116.90 (12) |
N1—C2—H2 | 124.3 | C36—C35—C34 | 118.60 (16) |
C2—C3—O4 | 105.74 (15) | C36—C35—H35 | 120.7 |
C2—C3—C31 | 136.40 (15) | C34—C35—H35 | 120.7 |
O4—C3—C31 | 117.85 (12) | C35—C36—C31 | 121.79 (15) |
C32—C31—C36 | 118.14 (15) | C35—C36—H36 | 119.1 |
C32—C31—C3 | 120.94 (14) | C31—C36—H36 | 119.1 |
C36—C31—C3 | 120.92 (13) | C5—O4—C3 | 104.25 (11) |
C31—C32—C33 | 121.46 (16) | N1—C5—N5 | 127.66 (15) |
C31—C32—H32 | 119.3 | N1—C5—O4 | 115.48 (14) |
C33—C32—H32 | 119.3 | N5—C5—O4 | 116.82 (12) |
C32—C33—C34 | 117.52 (14) | C5—N5—H5A | 122.0 (17) |
C32—C33—H33 | 121.2 | C5—N5—H5B | 120.1 (14) |
C34—C33—H33 | 121.2 | H5A—N5—H5B | 118 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5A···N1i | 0.84 (3) | 2.12 (3) | 2.947 (2) | 165 (3) |
Symmetry code: (i) −x+1, −y+2, −z+2. |